Find Cheap Flights from Hawaii to Chicago

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Book cheap flights from Hawaii to Chicago (round-trip)

Airports
Origin
Kahului
$596
only
$596
Honolulu
$591
only
$591
Kailua-Kona
$817
only
$817
Destination
Chicago
$591
only
$591
$833
only
$833
Wed, May 2
HNL
ORD
12h 57m
Tue, May 15
ORD
HNL
20h 04m
Trip: 14 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

PHL
AMS
Okay 4.6

Fo

DFW
SAT
Okay 4.0

It was short

Completely full plane. Ridiculously tight seat pitch. Overhead bins full. 45-minute delay for a dead-heading flight crew. Long wait for checked baggage. No beverage service because of turbulence. Flight crew out of position is a management problem, don't make it an inconvenience for a 737 full of paying passengers!

BWI
CLT
Mediocre 3.0

One of the flight attendants was nice.

AA is now trying to save money (presumably) by doing like Delta: forcing half of us to connect in Charlotte. Unfortunately, the Charlotte airport is not ready to accommodate so many people. The airport looks like it is being renovated, which is fine, but there is no tape/cones to mark off the renovated areas from the walkways. You literally walk through dirt and construction sites. I didn't even think that was legal in the US?! Anyway, maybe it will be worth it once the renovations are complete, especially if AA is going to use it as a hub.

HKG
BKK
Good 6.0

Flight delayed by 35 minutes

Fri, May 4
OGG
ORD
8h 00m
Sun, May 6
ORD
OGG
12h 41m
Trip: 3 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 2 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
LAX
ORD
Good 7.0

Crew was nice

Plane was delayed for 4 hours, should have given us miles or a voucher

EWR
TPA
Excellent 8.0

Made up time for delayed departure

So cramped. Sat next to very obese person....spilled onto my seat

OGG
ORD
Okay 4.0

AFTER boarding, you endeavored to remove 41 passengers. Only interaction was through an overwhelmed flight attendant, who barely spoke english. Was an experience that eroded confidence in safety, something one would imagine from a third world airline. Unacceptable. No direction. Only instruction was to call United.

MUC
IAD
Excellent 9.6

Flexibility in changing reservation at the last minute. Excellent service on board, good food.

PWM
IAD
Mediocre 2.0

Nothing was good about this airline with the exception of the baggage crew that finally helped me in Washington Ronald Regan Airport

My flight out of Portland was canceled and it took hours to rebook. I had to fly American Airline to Washington DCA where I roamed the airport at 9pm looking for someone from United. The crew in Portland ME told me the gate person would have a hotel for me.... The baggage crew had to help me.

Tue, May 8
OGG
ORD
11h 10m
Thu, May 31
ORD
OGG
31h 50m
Trip: 24 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 4
HNL
ORD
11h 34m
Tue, Aug 28
ORD
HNL
25h 05m
Trip: 56 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

SJC
SJD
Okay 4.6

poor

Tue, Mar 27
KOA
ORD
16h 33m
Fri, Apr 6
ORD
KOA
14h 03m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Mon, May 14
HNL
ORD
12h 30m
Sun, May 20
ORD
HNL
19h 59m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.6

Fo

DFW
DEN
Excellent 10.0

Easy and quick boarding. Excellwnt service in first class. Comfortable ride.

Nothing. Excellent travel experience.

LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

BWI
CLT
Mediocre 3.0

One of the flight attendants was nice.

AA is now trying to save money (presumably) by doing like Delta: forcing half of us to connect in Charlotte. Unfortunately, the Charlotte airport is not ready to accommodate so many people. The airport looks like it is being renovated, which is fine, but there is no tape/cones to mark off the renovated areas from the walkways. You literally walk through dirt and construction sites. I didn't even think that was legal in the US?! Anyway, maybe it will be worth it once the renovations are complete, especially if AA is going to use it as a hub.

DFW
SAT
Okay 4.0

It was short

Completely full plane. Ridiculously tight seat pitch. Overhead bins full. 45-minute delay for a dead-heading flight crew. Long wait for checked baggage. No beverage service because of turbulence. Flight crew out of position is a management problem, don't make it an inconvenience for a 737 full of paying passengers!

Sat, Mar 10
OGG
ORD
7h 51m
Wed, Mar 14
ORD
OGG
14h 26m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Apr 23
HNL
ORD
8h 13m
Tue, May 1
ORD
HNL
9h 12m
Trip: 9 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 36 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
HNL
ORD
Excellent 8.5

Flight attendants were great! Friendly, efficient, and helpful. Power outlets are outstanding.

Luggage pick up was delayed. And the constant selling of products during the flight. Come on, a nine hour flight should have complimentary WiFi in this day and age. Also, few people want to pay for on board for airline food.

HNL
ORD
Okay 5.6

No WiFi. The new United system is worthless on most flights.

Entertainment and food.

HNL
ORD
Good 7.6

Ground Stall and flight attendants were unusually pleasant. Perhaps the recent bad press United has been receiving had something to do with the turn around. All for the better. Keep up the good work.

As usual, plane was crowded and seats were uncomfortable, even in economy plus.

HNL
ORD
Okay 5.6

No delays, nice personnel and food pas OK but a little pricy.

Internet costing 8$ for an hour is way overpriced, no leg room, seats not really comfy, no meals provided during an 8 hour flight.

HNL
ORD
Excellent 8.0

paid for extra legroom and it made a difference. Staff was very responsive.

Cabin temperature fluctuated quite a bit

Tue, Apr 24
HNL
ORD
15h 59m
Sat, Apr 28
ORD
HNL
19h 03m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ORD
MCO
Mediocre 2.6

Horribly made me cancel flight because of 1min after 30 min cut off for boarding pass. Sat at the front desk for 29 minute arguing until my plane left.

LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

DFW
SAT
Okay 4.0

It was short

Completely full plane. Ridiculously tight seat pitch. Overhead bins full. 45-minute delay for a dead-heading flight crew. Long wait for checked baggage. No beverage service because of turbulence. Flight crew out of position is a management problem, don't make it an inconvenience for a 737 full of paying passengers!

DFW
DEN
Excellent 10.0

Easy and quick boarding. Excellwnt service in first class. Comfortable ride.

Nothing. Excellent travel experience.

PHL
AMS
Okay 4.6

Fo

Tue, Jun 5
HNL
ORD
11h 20m
Tue, Jun 12
ORD
HNL
13h 36m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 19
HNL
MDW
13h 01m
Sat, Apr 21
MDW
HNL
16h 20m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 9.6

Z

Tue, Jul 10
HNL
ORD
27h 35m
Thu, Aug 23
ORD
HNL
20h 25m
Trip: 45 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

SEA
MCO
Mediocre 2.3

I dispatched a guitar in a hard case. It was labeled fragile and sent to a separate compartment. The guitar was poorly treated and the case was broken all over. Very disappointing. On top of that I had requested window seat and got the middle seat. No food was served and there was no movies to watch or anything, considering this was a five hour flight

SJC
SJD
Okay 4.6

poor

SEA
DEN
Excellent 10.0

boarding was late due to repairs on the plane

SEA
SNA
Excellent 9.3

Up and down, no problems

Chocolate and almonds for breakfast snack?

Thu, Mar 1
HNL
ORD
12h 38m
Thu, Mar 15
ORD
HNL
21h 08m
Trip: 14 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
HNL
ORD
19h 27m
Tue, Jun 12
ORD
HNL
21h 07m
Trip: 8 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
SNA
Excellent 9.3

Up and down, no problems

Chocolate and almonds for breakfast snack?

RDU
SEA
Excellent 8.3

The flight crew was incredibly sweet and helpful; one of them even gave me their personal TUMS when I said I didn't feel well.

The flight boarded 30 minutes early; I arrived to my gate at the time of when my ticket said boarding started, but they were already calling final boarding call for my flight. I completely panicked. The plane was clean but the seats are very close together and there were no complimentary snacks- even though it was a 6 hour flight. On my flight back from Seattle on Delta, we got a complimentary meal AND a complimentary snack. I was expecting my Alaskan flight to be better based on everything I'd heard from friends, but my return Delta flight showed Alaska up; it was a spacier plane with way more food offered.

SJC
SJD
Okay 4.6

poor

SEA
DEN
Excellent 10.0

boarding was late due to repairs on the plane

FAI
SEA
Excellent 9.6

Easy on off and let us sleep

Mon, May 7
HNL
MDW
16h 03m
Sat, May 12
MDW
HNL
16h 10m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

JFK
CDG
Excellent 10.0

The food and the service

Sun, Mar 18
HNL
ORD
8h 03m
Sun, Apr 1
ORD
HNL
31h 16m
Trip: 15 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 36 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
HNL
ORD
Good 7.6

Ground Stall and flight attendants were unusually pleasant. Perhaps the recent bad press United has been receiving had something to do with the turn around. All for the better. Keep up the good work.

As usual, plane was crowded and seats were uncomfortable, even in economy plus.

HNL
ORD
Mediocre 3.3

Flight was timely

We flew to Hawaii for a friend's wedding and many of us flew different airlines. You would think that a flight that was 8 hours would include a meal?! Our friends who flew Delta and American all got meals and snacks. Another issue too is that you do get free movies although they don't tell you as your boarding that you would need their App to watch it. So if you didn't download it before take off you have to pay for their internet or their tablet.

HNL
ORD
Excellent 8.5

Flight attendants were great! Friendly, efficient, and helpful. Power outlets are outstanding.

Luggage pick up was delayed. And the constant selling of products during the flight. Come on, a nine hour flight should have complimentary WiFi in this day and age. Also, few people want to pay for on board for airline food.

HNL
ORD
Okay 5.6

No WiFi. The new United system is worthless on most flights.

Entertainment and food.

HNL
ORD
Excellent 8.6

Wifi coverage was not reliable

Fri, Jun 8
OGG
ORD
11h 35m
Thu, Jun 14
ORD
OGG
19h 55m
Trip: 7 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
RDU
SEA
Excellent 8.3

The flight crew was incredibly sweet and helpful; one of them even gave me their personal TUMS when I said I didn't feel well.

The flight boarded 30 minutes early; I arrived to my gate at the time of when my ticket said boarding started, but they were already calling final boarding call for my flight. I completely panicked. The plane was clean but the seats are very close together and there were no complimentary snacks- even though it was a 6 hour flight. On my flight back from Seattle on Delta, we got a complimentary meal AND a complimentary snack. I was expecting my Alaskan flight to be better based on everything I'd heard from friends, but my return Delta flight showed Alaska up; it was a spacier plane with way more food offered.

SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

SEA
DEN
Excellent 10.0

boarding was late due to repairs on the plane

EWR
SJC
Good 6.0

Felt much longer than it needed to be - 7 hours?

Wed, Mar 21
HNL
ORD
8h 03m
Mon, Apr 2
ORD
HNL
31h 19m
Trip: 13 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Aug 30
HNL
ORD
8h 10m
Mon, Sep 3
ORD
HNL
13h 55m
Trip: 5 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 36 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
HNL
ORD
Excellent 8.5

Flight attendants were great! Friendly, efficient, and helpful. Power outlets are outstanding.

Luggage pick up was delayed. And the constant selling of products during the flight. Come on, a nine hour flight should have complimentary WiFi in this day and age. Also, few people want to pay for on board for airline food.

HNL
ORD
Okay 5.6

No delays, nice personnel and food pas OK but a little pricy.

Internet costing 8$ for an hour is way overpriced, no leg room, seats not really comfy, no meals provided during an 8 hour flight.

HNL
ORD
Excellent 8.0

Speed and staff. Plane clean. Wife needs help and it was always there. Land people good as well.

No internet or movies.

HNL
ORD
Excellent 8.0

No food offered. Only received one drink serving.

HNL
ORD
Good 7.6

Ground Stall and flight attendants were unusually pleasant. Perhaps the recent bad press United has been receiving had something to do with the turn around. All for the better. Keep up the good work.

As usual, plane was crowded and seats were uncomfortable, even in economy plus.

Thu, Mar 1
HNL
MDW
13h 02m
Thu, Mar 15
MDW
HNL
16h 04m
Trip: 14 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

JFK
CDG
Excellent 10.0

The food and the service

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Hawaii to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Hawaii
Flight Price $591
Airlines American Airlines, United, Alaska Airlines, Delta
*
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